This invention relates to new chemical compounds. More particularly it relates to new chemical compounds which are of value as antibacterial agents. These new antibacterial agents are bis-esters of 4,5-di(hydroxymethyl)-2-oxo-1,3-dioxole, in which one hydroxy group has been esterified with the carboxy group of 6-(2-amino-2-phenylacetamido)penicillanic acid (ampicillin) or 6-(2-amino-2-[4-hydroxyphenyl]acetamido)penicillanic acid (amoxicillin), and the other hydroxy group has been esterified with the carboxy group of penicillanic acid 1,1-dioxide (sulbactam).
European patent application No. 39,086, published Nov. 4, 1981, discloses esters of 4-hydroxymethyl-2-oxo-1,3-dioxole, optionally further substituted at the 5-position, in which the hydroxy group has been esterified with the carboxy group of 6-(2-amino-2-phenylacetamino)penicillanic acid. U.S. Pat. No. 4,244,951 discloses bis-esters of methanediol in which one hydroxy group has been esterified with the carboxy group of certain 6-acrylaminopenicillanic acids and the other hydroxy group has been esterified using penicillanic acid 1,1-dioxide. In like manner, U.S. Pat. No. 4,359,472 discloses bis-esters of di(hydroxymethyl) carbonate with certain 6-acrylaminopenicillanic acid compounds and penicillanic acid 1,1-dioxide. Penicillanic acid 1,1-dioxide is known from U.S. Pat. No. 4,234,579 as an antibacterial agent and beta-lactamase inhibitor.
The antibacterial agents of the present invention are efficiently absorbed from the gastrointestinal tract of mammals, and after absorption they are transformed into 6-(2-amino-2-phenylacetamido)penicillanic acid (ampicillin) or 6-(2-amino-2-[4-hydroxyphenyl]acetamido)penicillanic acid (amoxicillin) and penicillanic acid 1,1-dioxide (sulbactam).